Classifications

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  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q19/00—Preparations for care of the skin
  • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
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  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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  • A61K8/37—Esters of carboxylic acids
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  • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
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  • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
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  • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
  • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
  • A61K8/492—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid having condensed rings, e.g. indol
• • A—HUMAN NECESSITIES
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• • A—HUMAN NECESSITIES
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  • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
  • A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
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  • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
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  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
  • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
  • C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
  • C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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  • C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
  • C07C243/26—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
  • C07C243/30—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton
  • C07C243/32—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton the carbon skeleton containing rings
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  • C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
  • C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
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  • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
  • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
  • C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
  • C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
  • C07C323/59—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton with acylated amino groups bound to the carbon skeleton
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  • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
  • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
  • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
  • C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
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  • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
  • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
  • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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  • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
  • C07D209/04—Indoles; Hydrogenated indoles
  • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
  • C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
  • C07D209/16—Tryptamines
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  • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
  • C07D209/04—Indoles; Hydrogenated indoles
  • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
  • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
  • C07D209/20—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals substituted additionally by nitrogen atoms, e.g. tryptophane
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  • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
  • C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
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  • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
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  • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
  • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
  • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
  • C07D295/182—Radicals derived from carboxylic acids
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  • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
  • C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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  • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
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  • C07C2601/14—The ring being saturated

Definitions

• the present invention relates to novel resorcinol-based compounds and to a cosmetic treatment process, in particular for depigmenting and/or bleaching the skin, employing such a compound.
• the mechanism of formation of the pigmentation of the skin that is to say of the formation of melanin, is particularly complex and involves, schematically, the following main stages:
• Tyrosinase (monophenol dihydroxyl phenylalanine: oxygen oxidoreductase EC 1 .14.18.1 ) is the essential enzyme involved in this sequence of reactions. In particular, it catalyses the conversion reaction of tyrosine to give Dopa (dihydroxyphenylalanine), by virtue of its hydroxylase activity, and the conversion reaction of Dopa to give dopaquinone, by virtue of its oxidase activity. This tyrosinase only acts when it is in the maturation state under the effect of certain biological factors.
• a substance is recognized as depigmenting if it acts directly on the vitality of the epidermal melanocytes where melanogenesis takes place and/or if it interferes with one of the steps of melanin biosynthesis, either by inhibiting one of the enzymes involved in melanogenesis or by being inserted as a structural analogue of one of the chemical compounds in the sequence for the synthesis of melanin, which sequence can then be blocked and thus ensure depigmentation.
• Arbutin and kojic acid are known as agents for depigmenting the skin.
• a subject of the invention is thus novel compounds of formula (I) as defined below.
• compositions comprising, in a physiologically acceptable medium, at least one compound of formula (I) as defined below.
• Another subject of the invention is a non-therapeutic cosmetic process for depigmenting, lightening and/or bleaching keratin materials, in particular the skin, comprising the application of the composition described above.
• the invention also relates to the non-therapeutic cosmetic use of a compound of formula (I) as an agent for bleaching, lightening and/or depigmenting keratin materials, in particular the skin.
• the compounds according to the invention make it possible to effectively depigment and/or lighten, indeed even to bleach, human skin. They are in particular intended to be applied to the skin of individuals exhibiting brownish pigmentation blemishes or blemishes due to ageing or to the skin of individuals desiring to combat the appearance of a brownish colour originating from melanogenesis.
• novel compounds according to the invention thus correspond to formula (I) below:
• R denotes a hydrogen atom or an acetyl group
• Y denotes a radical chosen from OR' and NAR"
• ' denotes a radical chosen from: a) -H;
• a saturated or unsaturated non-aromatic 5- to 8-membered heterocycle comprising one or more heteroatoms chosen from O, N and S, optionally substituted with one or more hydroxyls and/or with one or more C1 -C8 alkoxy or C1 -C4 alkyl radicals; one of the ring members possibly being a carbonyl group;
• a C5-C12 (hetero)aryl group optionally containing one or more heteroatoms chosen from O, N and S, optionally substituted with one or more hydroxyls and/or with one or more radicals chosen from C1 -C8 alkoxy and C1 -C8 alkyl groups;
• R5 being chosen from H, a saturated linear C1 -C10 or branched C3-C10 or unsaturated C2-C10 or cyclic C3-C8 alkyl hydrocarbon-based group;
• R6 and R7 which may be identical or different, being chosen from H, a saturated linear C1 -C10 or branched C3-C10 or unsaturated C2-C10 or cyclic C3-C8 alkyl hydrocarbon-based group; a (C1 - C4)alkyl(hetero)(C6)aryl group optionally containing a nitrogen atom, especially a benzyl group;
• R6 and R7 possibly forming, with the nitrogen atom that bears them, a 5- to 8-membered heterocycle which may contain one or more heteroatoms or groups chosen from
• A denotes a radical chosen from:
• x a saturated or unsaturated non-aromatic 5- to 8-membered heterocycle, comprising one or more heteroatoms chosen from O, N and
• a C5-C12 (hetero)aryl group optionally containing one or more heteroatoms chosen from O, N and S, optionally substituted with one or more hydroxyls and/or with one or more radicals chosen from C1 -C8 alkoxy
• R12 and R13 which may be identical or different, denoting a radical chosen from:
• R14 denoting a radical chosen from:
• a C5-C12 (hetero)aryl radical optionally containing one or more heteroatoms chosen from O, N and S, optionally substituted with one or more hydroxyls and/or with one or more C1 -C8 alkoxy radicals;
• a C5-C12 (hetero)aryl group optionally containing one or more heteroatoms chosen from O, N and S, optionally substituted with one or more hydroxyls and/or with one or more C1 -C8 alkoxy radicals;
• R15 being chosen from H, a saturated linear C1 -C10 or branched C3-
• R16 and R17 which may be identical or different, being chosen from H and a saturated linear C1 -C10 or branched C3-C10 or unsaturated C2- C10 or cyclic C3-C8 alkyl hydrocarbon-based group; a (C1 -
• C4)alkyl(hetero)(C6)aryl group optionally containing a nitrogen atom, especially a benzyl group; an acetyl radical; R16 and R17 possibly forming, with the nitrogen that bears them, a 5- to 8-membered heterocycle, which may contain one or more heteroatoms or groups chosen from N, O and -CO- and/or optionally substituted with a C1 -C10 hydrocarbon-based chain;
• ' denotes a radical chosen from: a) -H;
• a linear saturated C1 -C20 or unsaturated C2-C20 or branched C3-C20 or cyclic C3-C8 alkyl group optionally interrupted with one or more heteroatoms or groups chosen from N, O, -CO- or a combination thereof such as -NHCO- or -NHCONH-, and/or optionally substituted with one or more identical or different groups chosen from:
• a saturated or unsaturated non-aromatic 5- to 8-membered heterocycle comprising one or more heteroatoms chosen from O, N and S, optionally substituted with one or more hydroxyls and/or with one or more C1 -C8 alkoxy or C1 -C4 alkyl radicals; one of the ring members possibly being a carbonyl group;
• a C5-C12 (hetero)aryl group optionally containing one or more heteroatoms chosen from O, N and S, optionally substituted with one or more hydroxyls and/or with one or more radicals chosen from C1 -C8 alkoxy and C1 -C8 alkyl groups;
• R25 being chosen from H, a saturated linear C1 -C10 or branched C3- C10 or unsaturated C2-C10 or cyclic C3-C8 alkyl hydrocarbon-based group;
• R26 and R27 which may be identical or different, being chosen from H, a saturated linear C1 -C10 or branched C3-C10 or unsaturated C2-C10 or cyclic C3-C8 alkyl hydrocarbon-based group; a (C1 - C4)alkyl(hetero)(C6)aryl group optionally containing a nitrogen atom, especially a benzyl group; R26 and R27 possibly forming, with the nitrogen that bears them, a 5- to 8-membered heterocycle, which may contain one or more heteroatoms or groups chosen from N, O and -CO- and/or optionally substituted with a C1 -C10 hydrocarbon-based chain; it being understood that A and R" may form, with the nitrogen atom that bears them, a saturated or unsaturated 5- to 8-membered heterocycle, which may contain one or more heteroatoms or groups chosen from N, O and -CO- and/or optionally substituted with a C1 -C10 hydrocarbon-
• radical (1 ) When a radical (1 ) may be substituted with one or more radicals (2) as specified previously, preferentially, the said radical (1 ) may be substituted with 1 to 3 radicals (2) as specified previously.
• a cyclic radical (1 ') optionally contains one or more heteroatoms or groups as specified previously, preferentially, the said cyclic radical (1 ') optionally contains 1 to 3 heteroatoms or groups as specified previously.
• the salts of the compounds of formula (I) comprise conventional non-toxic salts of the said compounds, such as those formed from acid or base. Mention may be made, as salts of the compound of formula (I) (when it comprises a quaternizable nitrogen atom), of: a) the salts obtained by addition of the compound (I) to a mineral acid, chosen in particular from hydrochloric, boric, hydrobromic, hydriodic, sulfuric, nitric, carbonic, phosphoric or tetrafluoroboric acid;
• the salts obtained by addition of the compound (I) to an organic acid chosen in particular from acetic, propionic, succinic, fumaric, lactic, glycolic, citric, gluconic, salicylic, tartaric, terephthalic, methylsulfonic, ethylsulfonic, benzenesulfonic, toluenesulfonic or triflic acid.
• organic acid chosen in particular from acetic, propionic, succinic, fumaric, lactic, glycolic, citric, gluconic, salicylic, tartaric, terephthalic, methylsulfonic, ethylsulfonic, benzenesulfonic, toluenesulfonic or triflic acid.
• salts obtained by addition of the compound of formula (I) (when it comprises an acid group) to an mineral base such as sodium hydroxide, potassium hydroxide, calcium hydroxide, ammonium hydroxide, magnesium hydroxide, lithium hydroxide, and the carbonates or hydrogen carbonates of sodium, of potassium or of calcium, for example;
• a primary, secondary or tertiary alkylamine for example triethylamine or butylamine.
• This primary, secondary or tertiary alkylamine can contain one or more nitrogen and/or oxygen atoms and can thus contain, for example, one or more alcohol functional groups; mention may in particular be made of 2-amino-2-methylpropanol, ethanolamine, triethanolamine, 2-(dimethylamino)propanol, 2-amino-2-(hydroxymethyl)-1 ,3- propanediol or 3-(dimethylamino)propylamine.
• salts of amino acids such as, for example, lysine, arginine, guanidine, glutamic acid or aspartic acid.
• the salts of the compound of formula (I) can be chosen from alkali metal or alkaline-earth metal salts, such as sodium, potassium, calcium or magnesium; or ammonium salts.
• the salts of the compound of formula (I) can be chosen from halides, such as chloride or bromide, citrate, acetate, succinate, phosphate, lactate or tartrate.
• the acceptable solvates of the compounds described in the present invention comprise conventional solvates, such as those formed during the preparation of the said compounds due to the presence of solvents. Mention may be made, by way of example, of the solvates due to the presence of water or of linear or branched alcohols, such as ethanol or isopropanol.
• optical isomers are in particular enantiomers and diastereoisomers.
• a "(Cx-Cy)alkyl group” denotes an alkyl group comprising from x to y carbon atoms.
• Such an alkyl group can be linear and saturated and can typically include from 1 to 20 carbon atoms or also from 1 to 10 carbon atoms. It can also be linear and unsaturated and can typically include from 2 to 20 carbon atoms or also from 2 to 10 carbon atoms. It can also be branched and can typically include from 3 to 20 carbon atoms or also from 3 to 10 carbon atoms.
• An alkyl group can also be cyclic; it is then a cycloalkyl group, which can typically include from 3 to 8 carbon atoms.
• a "(C x -C y )alkyl group” denotes a linear and saturated alkyl group comprising from x to y carbon atoms.
• the saturated or branched linear alkyl groups may be chosen from: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, 2-ethylhexyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl and eicosyl.
• the saturated or branched linear alkyl groups may be chosen from: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, 2-ethylhexyl and octyl.
• the cycloalkyl group may be chosen from: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.
• (Cx-Cy)alkoxy group denotes a linear and if appropriate branched group of formula -O(C x -C y )alkyl which can typically include from 1 to 8 carbon atoms or also from 1 to 4 carbon atoms.
• the alkoxy group may be chosen from methoxy, ethoxy, propoxy and butoxy and can more particularly be a methoxy group.
• a "saturated or unsaturated non-aromatic heterocycle group” denotes a monocyclic or bicyclic carbocyclic 5- to 8-membered group containing one to three heteroatoms or groups chosen from N, O, S and -C(O)-.
• a heterocycle group may be chosen from piperidyl, morpholinyl, piperazinyl and pyrrolidinyl. Preferentially, it is the piperidyl or morpholinyl ring.
• aryl group denotes an unsaturated or partially unsaturated monocyclic or bicyclic carbocyclic group including from 5 to 12 carbon atoms.
• the aryl radicals may be chosen from phenyl, naphthyl, indenyl, fluorenyl and anthracenyl. Preferably, it is the phenyl group.
• heteroaryl group denotes a fused or non-fused, 5- to 22-membered monocyclic or polycyclic group, comprising from 1 to 6 heteroatoms chosen from nitrogen, oxygen and sulfur, and at least one ring of which is aromatic; preferentially, a heteroaryl radical is chosen from acridinyl, benzimidazolyl, benzobistriazolyl, benzopyrazolyl, benzopyridazinyl, benzoquinolyl, benzothiazolyl, benzotriazolyl, benzoxazolyl, pyridyl, tetrazolyl, dihydrothiazolyl, imidazopyridyl, imidazolyl, indolyl, isoquinolyl, naphthimidazolyl, naphthxazolyl, naphthpyrazolyl, oxadiazolyl, oxazolyl, oxazolopyridyl, phenazinyl,
• 5- to 8-membered heterocycle which may contain one or more heteroatoms or groups chosen from N and O
• N and O means in particular, in a non- limiting manner, piperidine, morpholine, piperazine, imidazole and pyrrolidine rings. Preferentially, it is a piperidine or morpholine ring.
• the compounds of formula (I) have the following meanings: R denotes a hydrogen atom or an acetyl group;
• Y denotes a radical chosen from OR' and NAR"
• R' denotes a radical chosen from: a) -H;
• a linear saturated C1 -C10 or unsaturated C2-C10 or branched C10 or cyclic C3-C8 alkyl group optionally interrupted with one or more heteroatoms or groups chosen from N, O, -CO- or a combination thereof such as -NHCO- or -NHCONH-, and/or optionally substituted with one or more groups -OR15; R15 being chosen from H and a saturated linear C1 -C4 alkyl hydrocarbon-based group;
• a C5-C12 (hetero)aryl group optionally containing one or more heteroatoms chosen from O, N and S, optionally substituted with one or more hydroxyls and/or with one or more radicals chosen from C1 -C8 alkoxy and C1 -C8 alkyl groups;
• A denotes a radical chosen from:
• a saturated or unsaturated non-aromatic 5- to 8-membered heterocycle comprising one or more heteroatoms chosen from O, N and S, optionally substituted with one or more hydroxyls and/or with one or more C1 -C8 alkoxy or C1 -C4 alkyl radicals; one of the ring members possibly being a carbonyl group;
• a C5-C12 (hetero)aryl group optionally containing one or more heteroatoms chosen from O, N and S, optionally substituted with one or more hydroxyls and/or with one or more radicals chosen from C1 -C8 alkoxy and C1 -C8 alkyl groups;
• R12 and R13 which may be identical or different, denoting a radical chosen from:
• a phenyl group optionally substituted with one or more hydroxyls and/or with one or more C1 -C8 alkoxy radicals;
• R12 and R13 possibly forming, with the nitrogen that bears them, a 5- to 8-membered heterocycle, which may contain one or more heteroatoms or groups chosen from N, O and -CO- and/or optionally substituted with a
• C1 -C10 hydrocarbon-based chain optionally containing one or more radicals chosen from hydroxyl and C1 -C4 alkoxy;
• R14 denoting a radical chosen from:
• R15 being chosen from H, a saturated linear C1 -C10 or branched C3- C10 or unsaturated C2-C10 or cyclic C3-C8 alkyl hydrocarbon-based group;
• R16 and R17 which may be identical or different, being chosen from H and a saturated linear C1 -C10 or branched C3-C10 or unsaturated C2- C10 or cyclic C3-C8 alkyl hydrocarbon-based group; a (C1 - C4)alkyl(hetero)(C6)aryl group optionally containing a nitrogen atom, especially a benzyl group; an acetyl radical;
• R16 and R17 possibly forming, with the nitrogen that bears them, a 5- to 8-membered heterocycle, which may contain one or more heteroatoms or groups chosen from N, O and -CO- and/or optionally substituted with a C1 -C10 hydrocarbon-based chain; otes a radical chosen from: a) -H;
• a and R" may form, with the nitrogen atom that bears them, a saturated or unsaturated 5- to 8-membered heterocycle, which may contain one or more heteroatoms or groups chosen from N, O and -CO- and/or optionally substituted with a C1 -C4 hydrocarbon-based chain or C1 -C4 hydroxyalkyl or CO2T, T denoting a hydrogen atom or a saturated linear C1 -C6 or branched C3-C6 alkyl radical, and the salts thereof, the solvates thereof, the optical isomers thereof and the racemic mixtures thereof, alone or as a mixture.
• ⁇ R denotes a hydrogen atom
• Y denotes a radical chosen from OR' and NAR"
• R' denotes a radical chosen from: a) -H;
• A denotes a radical chosen from:
• -COOR16 ix) a C5-C12 (hetero)aryl group, optionally containing one or more heteroatoms chosen from O, N and S, optionally substituted with one or more hydroxyls and/or with one or more C1 -C8 alkoxy radicals;
• x a saturated or unsaturated non-aromatic 5- to 8-membered heterocycle, comprising one or more heteroatoms chosen from O, N and
• a phenyl group optionally substituted with one or more radicals chosen from hydroxyl and/or methoxy and/or ethoxy;
• R12 and R13 which may be identical or different, denoting a radical chosen from:
• a phenyl group optionally substituted with one or more hydroxyls and/or with one or more C1 -C8 alkoxy radicals;
• R14 denoting a radical chosen from:
• R15 being chosen from H and a saturated linear C1 -C4 or branched C3-C4 alkyl hydrocarbon-based group
• R16 and R17 which may be identical or different, being chosen from H and a saturated linear C1 -C10 or branched C3-C10 or unsaturated C2-C10 or cyclic C3-C8 alkyl hydrocarbon-based group; a (C1 -C4)alkyl(hetero)(C6)aryl group optionally containing a nitrogen atom, especially a benzyl group; an acetyl radical; R16 and R17 possibly forming, with the nitrogen that bears them, a 5- to 8- membered heterocycle, which may contain one or more heteroatoms or groups chosen from N, O and -CO- and/or optionally substituted with a C1 -C10 hydrocarbon-based chain; R" denotes a radical chosen from: a) -H;
• a linear saturated C1 -C10 or branched C3-C10 alkyl group optionally substituted with one or more identical or different groups -OR25;
• R25 being chosen from H and a saturated linear C1 -C4 alkyl hydrocarbon- based group;
• a and R" may form, with the nitrogen atom that bears them, a saturated or unsaturated 5- to 8-membered heterocycle, which may contain one or more heteroatoms or groups chosen from N, O and -CO- and/or optionally substituted with a C1 -C4 hydrocarbon-based chain or C1 -C4 hydroxyalkyl or CO2T, T denoting a hydrogen atom or a saturated linear C1 -C6 or branched C3-C6 alkyl radical; and the salts thereof, the solvates thereof, the optical isomers thereof and the racemic mixtures thereof, alone or as a mixture.
• the particularly preferred products are chosen from:
• the most particularly preferred compounds in the context of the present invention are the following: compounds 1 to 6, 12 to 25, 31 , 33 and 59, and salts thereof, solvates thereof, isomers thereof and racemic mixtures thereof, taken alone or as a mixture.
• the compounds of the invention of formula (I) may be prepared according to the following synthetic routes:
• Resorcinol (A1 ) is reacted with itaconic acid (B) or its anhydride ( ⁇ ') or one of its esters of formula (B1 )
• R denotes H or a linear C1 -C6 or branched C3-C6 alkyl group, to form a compound C, and this compound is then activated to form a heterocycle of formula (III), which is then subjected to a reduction step to form the intermediate (IV) which gives access to the compounds (V).
• the intermediate of formula (IV) may also be accessed directly by reacting resorcinol (A1 ) with tulipaline (3-methylenedihydrofuran-2-one) (A2).
• This step makes it possible to arrive directly at the compounds of formula (I) by reaction of derivatives YH.
• One variant consists in treating (IV) with an alcohol ROH to give the compounds (V), which, by reaction with YH, lead to (I).
• reaction of resorcinol (A1 ) in the presence of itaconic acid (B) or its anhydride ( ⁇ ') or one of its esters of formula (B1 ) which are described above, in order to form the compound C is especially performed in the presence of an organic solvent which may be chosen from toluene, tetrahydrofuran, heptane, isooctane, methyltetrahydrofuran, methyl ethyl ketone, methyl isobutyl ketone, dioxane, ethyl acetate, isopropyl acetate, isododecane and mixtures thereof, in particular at a temperature of between 15 and 200°C, optionally in the presence of a catalyst (acidic or basic) as described in the publications: Synthesis of 7- hydroxycoumarins via the Pechmann reaction using Nafion resin/silica nanocomposites as catalysts: Laufer MC, Hausmann H and Holderich WF,
• the compounds (B1 ) may be obtained in a known way by selective esterification in an acidic medium of itaconic acid with one or more alcohols of formula ROH, as described in the literature (Selective esterification of non- conjugated carboxylic acids in the presence of conjugated or aromatic carboxylic acids over active carbon supported methanesulfonic acid; Feng, Ze Wang, Zhao, Xin Qi and Bi, Hua, Science in China, Series B: Chemistry (2008), 1 (10), 990-992 / An efficient and regiospecific estenfication of dioic acids using PTSA; Devi, A.
• the compound of formula (I) may be obtained by activation of the acid C according to the known acid activation methods, described especially in Comprehensive Organic Transformations by R. Larock, published by Wiley VCH, in the chapter Interconversion of nitriles, carboxylic acids and derivatives.
• Compound C in acid form is then esterified in the presence of ethanol under standard conditions of heating (between 15 and 100°C) and of acid catalysis to give a carboxylic acid ethyl ester derivative (A3), which, when activated according to the known acid activation methods, described especially in Comprehensive Organic Transformations by R.
• the reaction of resorcinol (A1 ) in the presence of tulipaline (3-methylene- dihydrofuran-2-one) (A2), and leading to compound (IV), is especially performed in the presence of an organic solvent which may be chosen from toluene, tetrahydrofuran, heptane, isooctane, m ethyl tetrahydrofu ran, methyl ethyl ketone, methyl isobutyl ketone, dioxane, ethyl acetate, isopropyl acetate and isododecane, and mixtures thereof, especially at a temperature of between 15 and 200°C, optionally in the presence of a catalyst (acidic or basic) as described in the publications: Synthesis of 7-hydroxycoumarins by Pechmann reaction using Nafion resin/silica nanocomposites as catalysts: Laufer MC, Hausmann H and Holderich WF, J.
• an organic solvent which
• an organic solvent in particular tetrahydrofuran, dioxane, dimethylformamide, dimethyl sulfoxide, 2- methyltetrahydrofuran, dichloromethane, toluene, methanol or ethanol, optionally in the presence of a catalyst chosen from acid catalysts of Lewis or Bronsted type or basic catalysts, such as potassium carbonate, triethylamine or diisopropylethylamine;
• the lactone (IV) may be in equilibrium with the ethyl ester form (IV) in the presence of ethanol.
• the acyclic ester can then react with YH compounds in order to result in the compounds (I).
• a catalyst chosen from acid catalysts of Lewis or Bronsted type or basic catalysts, such as potassium carbonate, triethylamine or diisopropylethylamine;
• the acetylation reaction may be carried out with acetic anhydride or acetyl chloride, in particular in the presence of an aprotic solvent, such as toluene, pyridine or tetrahydrofuran.
• an aprotic solvent such as toluene, pyridine or tetrahydrofuran.
• the acetylation reaction may be selective by employing protective groups on the functional groups which must not be acetylated and by then carrying out a deprotection reaction, according to the known techniques of organic synthesis.
• a mixed anhydride for example by using a C2-C6 alkyl chloroformate, such as isobutyl chloroformate, in the presence of a base, for instance triethylamine or diisopropylethylamine, ;
• these compounds may be obtained by saponification using mineral bases, for instance NaOH or LiOH, in the presence of protic or aprotic solvents, for instance ethanol or tetrahydrofuran or water, at temperatures ranging between 0 and 100°C.
• the salts obtained are then re-acidified in the presence of conventional mineral or organic acids, for instance hydrochloric acid or citric acid.
• the compounds of formula (I) according to the invention have a very particular application in the cosmetics field.
• composition according to the invention comprises, in a physiologically acceptable medium, a compound of formula (I) as described above.
• physiologically acceptable medium is understood to mean a medium that is compatible with human keratin materials, such as bodily skin or facial skin, the lips, mucous membranes, the eyelashes, the nails, the scalp and/or the hair.
• Compound (I) may be present in the composition according to the invention in an amount that may be between 0.01 % and 10% by weight, preferably between 0.1 % and 5% by weight and especially from 0.5% to 3% by weight relative to the total weight of the composition.
• composition according to the invention is advantageously a cosmetic composition: it can comprise adjuvants normally employed in the cosmetics field.
• Mention may especially be made of water, organic solvents, in particular C2-C6 alcohols, oils, especially hydrocarbon-based oils or silicone oils, waxes, pigments, fillers, dyes, surfactants, emulsifiers, cosmetic active agents, UV screening agents, polymers, thickeners, preserving agents, fragrances, bactericides, odour absorbers or antioxidants.
• oils especially hydrocarbon-based oils or silicone oils, waxes, pigments, fillers, dyes, surfactants, emulsifiers, cosmetic active agents, UV screening agents, polymers, thickeners, preserving agents, fragrances, bactericides, odour absorbers or antioxidants.
• optional cosmetic adjuvants may be present in the composition in a proportion of 0.001 % to 80% by weight and especially 0.1 % to 40% by weight relative to the total weight of the composition.
• these adjuvants, and the proportions thereof, will be chosen by a person skilled in the art so that the advantageous properties of the compounds according to the invention are not, or not substantially, adversely affected by the envisaged addition.
• retinol and derivatives thereof such as retinyl palmitate; ascorbic acid and derivatives thereof, such as magnesium ascorbyl phosphate and ascorbyl glucoside; tocopherol and derivatives thereof, such as tocopheryl acetate; nicotinic acid and precursors thereof, such as nicotinamide; ubiquinone; glutathione and precursors thereof, such as L-2-oxothiazolidine-4-carboxylic acid; plant extracts, and in particular plant proteins and hydrolysates thereof, and also phytohormones; marine extracts, such as algal extracts; bacterial extracts; sapogenins such as diosgenin and extracts of wild yam containing the same; ceramides; hydroxy acids, such as salicylic acid and 5-n-octanoylsalicylic acid; resveratrol; oligopeptides and pseudodipeptides and acylated derivatives thereof;
• treating agent is understood to mean any compound capable of having an effect:
• ⁇ -hydroxy acids in particular salicylic acid and its derivatives (including 5-(n- octanoyl)salicylic acid); cc-hydroxy acids, such as glycolic, citric, lactic, tartaric, malic or mandelic acid; urea; gentisic acid; oligofucoses; cinnamic acid; Saphora japonica extract; or resveratrol;
• corneodesmosomes such as glycosidases, stratum corneum chymotryptic enzyme (SCCE) or indeed even other proteases (trypsin, chymotrypsin-like).
• SCCE stratum corneum chymotryptic enzyme
• trypsin, chymotrypsin-like enzymes involved in desquamation or decomposition of the corneodesmosomes, such as glycosidases, stratum corneum chymotryptic enzyme (SCCE) or indeed even other proteases (trypsin, chymotrypsin-like).
• SCCE stratum corneum chymotryptic enzyme
• agents which chelate mineral salts include EDTA; N-acyl- ⁇ , ⁇ ', ⁇ '-ethylenediaminetriacetic acid; aminosulfonic compounds, in particular N-(2-hydroxyethyl)piperazine-N-2-ethanesulfonic acid (HEPES); 2- oxothiazolidine-4-carboxylic acid (procysteine) derivatives; derivatives of a-amino acids of glycine type (such as described in EP 0 852 949, and also sodium methyl glycine diacetate, sold by BASF under the trade name Trilon M); honey; or sugar derivatives, such as O-octanoyl-6-D-maltose and N- acetylglucosamine.
• the desquamating agents are generally present in the composition according to the invention in proportions ranging from 0.01 % to 15% by weight and preferably ranging from 0.1 % to 10% by weight relative to the total weight of the composition.
• pentacyclic triterpenes and extracts of plants comprising the same, such as ⁇ -glycyrrhetinic acid and its salts and/or its derivatives (glycyrrhetinic acid monoglucuronide, stearyl glycyrrhetinate, 3-(stearoyloxy)glycyrrhetic acid), ursolic acid and its salts, oleanolic acid and its salts, betulinic acid and its salts, a Paeonia suffruticosa and/or lactiflora extract, salicylic acid salts and in particular zinc salicylate, phycosaccharides from the company Codif, a Laminaria saccharina extract, canola oil, bisabolol, camomile extracts, allantoin, Sepivital EPC (phosphosaccharides from the company Codif, a Laminaria saccharina extract, canola oil, bisabolol, camomile extract
• the calmatives are generally present in the composition according to the invention in proportions ranging from 0.01 % to 15% by weight and preferably ranging from 0.1 % to 10% by weight, relative to the total weight of the composition.
• the organic photoprotective agents are chosen in particular from anthranilates; cinnamic derivatives; dibenzoylmethane derivatives; salicylic derivatives; camphor derivatives; triazine derivatives, such as those described in patent applications US 4 367 390, EP 863 145, EP 517 104, EP 570 838, EP 796 851 , EP 775 698, EP 878 469, EP 933 376, EP 507 691 , EP 507 692, EP 790 243 and EP 944 624; benzophenone derivatives; ⁇ , ⁇ -diphenylacrylate derivatives; benzotriazole derivatives; benzalmalonate derivatives; benzimidazole derivatives; imidazolines; bis-benzazolyl derivatives, such as
• the mineral photoprotective agents may be chosen in particular from coated or non-coated metal oxide pigments or nanopigments (mean size of the primary particles generally of between 5 nm and 100 nm, preferably between 10 nm and 50 nm), for instance titanium oxide (amorphous or crystallized in rutile and/or anatase form), iron oxide, zinc oxide, zirconium oxide or cerium oxide nanopigments, which are all well-known UV photoprotective agents.
• Conventional coating agents are furthermore alumina and/or aluminium stearate.
• Such coated or non-coated metal oxide nanopigments are described in particular in patent applications EP 518 772 and EP 518 773.
• the photoprotective agents are generally present in the composition according to the invention in proportions ranging from 0.1 % to 20% by weight and preferably ranging from 0.2% to 15% by weight relative to the total weight of the composition.
• composition according to the invention may be in any galenical form normally used in the cosmetics field and in particular in the form of an aqueous or aqueous/alcoholic solution, which is optionally gelled, a dispersion of the lotion type, optionally comprising two phases, an oil-in-water or water-in-oil or multiple (W/O/W or O/W/O, for example) emulsion, an aqueous gel, a dispersion of oil in an aqueous phase using spherules, it being possible for these spherules to be polymeric nanoparticles, such as nanospheres and nanocapsules or better still lipid vesicles of ionic and/or nonionic type, or an aqueous or oily gel.
• aqueous or aqueous/alcoholic solution which is optionally gelled
• a dispersion of the lotion type optionally comprising two phases, an oil-in-water or water-in-oil or multiple (W/O/W
• compositions are prepared according to the usual methods.
• Use is preferably made, according to this invention, of a composition in the form of an emulsion, in particular an oil-in-water emulsion.
• the composition according to the invention can constitute a composition for caring for the skin and in particular a cleansing, protecting, treating or care cream for the face, for the hands, for the feet, for the major anatomical folds or for the body (for example, day creams, night creams, make-up-removing creams, foundation creams or anti-sun creams); a fluid foundation; a make-up- removing milk, a protective or care body milk or an anti-sun milk; or a lotion, gel or mousse for caring for the skin, such as a cleansing lotion.
• methyltetrahydrofuran can be added in a sufficient amount to dissolve the reaction medium.
• the reaction medium is concentrated under vacuum.
• the crude product is dissolved in methyltetrahydrofuran, washed with a 0.1 N hydrochloric acid solution and then washed with water.
• the organic phase is collected, dried over magnesium sulfate and concentrated under vacuum.
• the crude product is purified on a chromatography column to give the expected product.
• Method 2 for obtaining the compounds (I) a) Production of the lactone (III) in acid form 10 g of resorcinol and 1 1 .8 g of itaconic acid were dissolved in 150 ml of a toluene/dioxane mixture (1/1 ratio by volume) in the presence of Amberlyst 15 resin from Aldrich in a round-bottomed flask equipped with a Dean and Stark apparatus. The reaction medium was heated at 100°C for 3 hours. After cooling, the crude reaction product was filtered and the filtrate was concentrated under vacuum. The crude product was recrystallized under hot conditions from ethyl acetate. 10 g of a white powder corresponding to the expected product were obtained (yield of 50%).
• the medium is concentrated under vacuum.
• the crude product is dissolved in methyltetrahydrofuran, washed with a 0.1 N hydrochloric acid solution and then washed with water.
• the organic phase is collected, dried over sodium sulfate and concentrated under vacuum.
• the crude product is purified on a chromatography column to give the expected product.
• Example 33 Example of separation of the diastereoisomers and characterization of the latter
• Compound 1 is subjected to a preferential crystallization in hot dichloromethane (20 volumes w/w). A diastereoisomer precipitates out (1 -a) during the temperature decrease. The second one is present in the filtrate (1 -b).
• Another method consists in and performing a separation using a preparative HPLC system.
• a biological test demonstrated the depigmenting activity of the compounds I.
• the modulating effect on melanogenesis of compound 1 was measured according to the method described in patent FR-A-2 734 825, and in the article by R. Schmidt, P. Krien and M. Regnier, Anal. Biochem., 235(2), 1 13-18, 1996. This test is carried out on a coculture of keratinocytes and melanocytes. For the test compound, the following were determined:
• the compounds according to the invention are thus shown to be effective in inhibiting melanogenesis and are furthermore more effective than arbutin and kojic acid.
• compositions comprising 300 ⁇ of compound 1 in DMSO were applied to samples of pigmented reconstructed epidermis (cf. EP 1 878 790).
• the control is DMSO.
• the melanin was quantified by image analysis on histological slices after staining with Fontana Masson dye. Each sample of coloured epidermis is photographed over its entire length using a camera connected to a microscope.
• the melanin is thresholded and the number of melanin pixels is measured in each field using automated image analysis software. A non-parametric statistical test is performed in order to determine the significance of the measurements (Mann-Whitney test).
• Example 35 Use of a cosmetic formulation
• a depigmenting gel for the skin comprising (% by weight):
• Carbomer (Carbopol 981 from Lubrizol) 1 %
• composition applied to the skin, makes it possible to attenuate brown blemishes.

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